CA2794251A1 - Emulsions useful in beverages - Google Patents
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- CA2794251A1 CA2794251A1 CA2794251A CA2794251A CA2794251A1 CA 2794251 A1 CA2794251 A1 CA 2794251A1 CA 2794251 A CA2794251 A CA 2794251A CA 2794251 A CA2794251 A CA 2794251A CA 2794251 A1 CA2794251 A1 CA 2794251A1
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- Chemical & Material Sciences (AREA)
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- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Non-Alcoholic Beverages (AREA)
- Edible Oils And Fats (AREA)
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
It has now been found that emulsions having a discrete phase volume fraction of 60% to 67% with excellent stability may be prepared using at least one low molecular weight surfactant. Such emulsions have high oil loading and a small mean particle size of less than 0.2 microns. Further, such emulsions may be used in beverages without weighting agents.
Description
Emulsions Useful in Beverages This application claims priority to US patent application serial number 12/748,013 fled March 26, 2010.
Field of Invention This invention relates to emulsions useful in beverages with a discrete phase volume fraction of 60% to 67% comprising at least one low molecular weight surfactant and having a mean particle size less than 0.2 microns, the method of making the emulsions, and compositions containing the emulsions.
Background of the Invention Quillaja is a surfactant extracted from the inner bark of soap bark trees, Quillaja Saponaria Molina, an evergreen native to Chile and Peru. Containing saponins, it is often used as a substitute for soap and as an agricultural spray adjuvant. Quillaja is also used in pharmaceuticals, food products, personal care products, and fire-fighting foams.
Weighting agents are used in a significant portion of the beverage emulsions on the market today. Weighting agents are undesirable in that they typically constitute about half the cost of the emulsion, have regulatory limits, cannot be used in natural beverages, and add to the complexity and length of processing the beverage. Without using a weighting agent, however, emulsions and their resulted beverages are very difficult to stabilize. Small particle size is one of the most important and difficult factors to achieve for non-weighted emulsions.
Small particle size is important for many emulsions, and is particularly beneficial for clear beverages and alcohol containing beverages.
Summary of the Invention It has now been found that emulsions having a discrete phase volume fraction of 60%
to 67% with excellent stability may be prepared using at least one low molecular weight surfactant. Such emulsions have high oil loading and a small mean particle size of less than 0.2 microns. Further, such emulsions may be produced and used in beverages without weighting agents.
As used herein, "discrete phase" is intended to mean the dispersed or non-continuous phase and is intended to include the oil phase and the LMW surfactant.
As used herein, "non-weighted" is intended to mean containing essentially no weighting agents. Weighting agents are well-known in the art and include without limitation brominated vegetable oil, damar gum, sucrose acetate isobutyrate (SAIB) and other sucrose esters, glycerol ester of wood rosin (ester gum), colophony, polyglycerol fatty acid esters, gum elemi, and glycerol esters of gum rosin.
As used herein, "quillaja solid extract" is intended to mean the solid portion of the quillaja containing the surface-active saponin which provides the emulsification property.
The term quillaja solid extract is not intended to paean liquid quillaja extract which contains the solid portion and water.
Low molecular weight surfactants is intended to include surfactants with an HLB
greater than 9 and an average molecular weight less than 10,000 Daltons.
As used herein, polysorbate is intended to mean polyoxyethylene (20) sorbitan niono-fatty acid esters or Tweens, a class of emulsifiers commercially available on the market as:
Tween 20 = polyoxyethylene (20) sorbitan monolaurate;
Tween 40 = polyoxyethylene (20) sorbitan monopalmitate;
Tween 60 = polyoxyethylene (20) sorbitan nmonostearate; and Tween 80 = polyoxyethylene (20) sorbitan monooleate.
Field of Invention This invention relates to emulsions useful in beverages with a discrete phase volume fraction of 60% to 67% comprising at least one low molecular weight surfactant and having a mean particle size less than 0.2 microns, the method of making the emulsions, and compositions containing the emulsions.
Background of the Invention Quillaja is a surfactant extracted from the inner bark of soap bark trees, Quillaja Saponaria Molina, an evergreen native to Chile and Peru. Containing saponins, it is often used as a substitute for soap and as an agricultural spray adjuvant. Quillaja is also used in pharmaceuticals, food products, personal care products, and fire-fighting foams.
Weighting agents are used in a significant portion of the beverage emulsions on the market today. Weighting agents are undesirable in that they typically constitute about half the cost of the emulsion, have regulatory limits, cannot be used in natural beverages, and add to the complexity and length of processing the beverage. Without using a weighting agent, however, emulsions and their resulted beverages are very difficult to stabilize. Small particle size is one of the most important and difficult factors to achieve for non-weighted emulsions.
Small particle size is important for many emulsions, and is particularly beneficial for clear beverages and alcohol containing beverages.
Summary of the Invention It has now been found that emulsions having a discrete phase volume fraction of 60%
to 67% with excellent stability may be prepared using at least one low molecular weight surfactant. Such emulsions have high oil loading and a small mean particle size of less than 0.2 microns. Further, such emulsions may be produced and used in beverages without weighting agents.
As used herein, "discrete phase" is intended to mean the dispersed or non-continuous phase and is intended to include the oil phase and the LMW surfactant.
As used herein, "non-weighted" is intended to mean containing essentially no weighting agents. Weighting agents are well-known in the art and include without limitation brominated vegetable oil, damar gum, sucrose acetate isobutyrate (SAIB) and other sucrose esters, glycerol ester of wood rosin (ester gum), colophony, polyglycerol fatty acid esters, gum elemi, and glycerol esters of gum rosin.
As used herein, "quillaja solid extract" is intended to mean the solid portion of the quillaja containing the surface-active saponin which provides the emulsification property.
The term quillaja solid extract is not intended to paean liquid quillaja extract which contains the solid portion and water.
Low molecular weight surfactants is intended to include surfactants with an HLB
greater than 9 and an average molecular weight less than 10,000 Daltons.
As used herein, polysorbate is intended to mean polyoxyethylene (20) sorbitan niono-fatty acid esters or Tweens, a class of emulsifiers commercially available on the market as:
Tween 20 = polyoxyethylene (20) sorbitan monolaurate;
Tween 40 = polyoxyethylene (20) sorbitan monopalmitate;
Tween 60 = polyoxyethylene (20) sorbitan nmonostearate; and Tween 80 = polyoxyethylene (20) sorbitan monooleate.
The number (20) following the polyoxyethylene part refers to the total number of oxyethylene -(CHZCH20)- groups found in the molecule. The number following the Tween part is related to the type of fatty acid associated with the polyoxyethylene sorbitan part of the molecule.
As used herein, oil-in-water emulsion is intended to mean an emulsion in which the oil is in the discrete phase and the water (aqueous) is the continuous phase.
All ratios, percent, and fractions are on a weight/weight basis and all temperatures are in degrees Celsius unless otherwise expressly stated.
All pressures, unless otherwise expressly stated, are as measured on the APV
homogenizer specified in the Examples section.
Brief Description of Figures Figure 1 depicts the particle size distribution of an emulsion containing 48.9 % by weight of five-fold (5X) orange oil. The curve with squares (^) is of the fresh emulsion with a mean particle size of 0.142 microns. The curve with the smooth line is of a 6-months old emulsion with a mean particle size of 0.151 microns.
Detailed Description of the Invention The present invention pertains to oil-in-water emulsions having a discrete phase volume fraction of 60% to 67% and prepared using at least one low molecular weight surfactant. Such emulsions have excellent emulsion stability, high load, and a small mean particle size of less than 0.2 microns, Further, such emulsions may be produced and used in beverages without a weighting agent.
The at least one low molecular weight (LMW) surfactant is present in an amount of from 2% to 25%, in one embodiment from 8% to 14%, and in yet another embodiment from 12% to 14% (wt/wt) based on the emulsion. In one embodiment, the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate, lecithin, sugar esters, esters of glycerin, and mixtures thereof. In another embodiment, the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate, lecithin, and mixtures thereof, in yet another embodiment is a mixture of quillaja solid extract and polysorbate, and in still another embodiment is a mixture of quillaja and polyoxyethylene (20) sorbitan nmonostearate (Tween 60).
The oil may be any oil used in emulsions, and in one embodiment used in beverage emulsions such as flavor, color, and/or nutrient containing oils, as well as any plant oil, and may be natural or synthetic. In one embodiment, the oil is a fruit oil such as orange oil. In another aspect, the oil contains a nutient such as Vitamin E. In still another embodiment, the oil contains an omega-III fatty acid. The oil is present in a discrete phase volume fraction of from 60 to 67 and in one embodiment is present in in a discrete phase volume fraction of from 62% to 65%. In one embodiment, the volume ratio of LMW surfactant to oil is from 1:2 to 1:5.
The volume fraction of the discrete phase is calculated as set forth in the Examples section.
The emulsion is an oil-in-water emulsion and in one aspect the ratio of the continuous phase to the discrete phase phase is from 40:60 to 33:67 (v/v) and in another embodiment from 38:62 to 35:65 (v/v). The emulsion has a high solids level (discrete phase), and in one embodiment such high solids emulsion may be stored as is and then diluted to the desired solids level with water or other aqueous solvent immediately before or during incorporation into the end use composition, such as a beverage. In the alternative, the high solids emulsion may be diluted prior to storage to enhance the stability.
As used herein, oil-in-water emulsion is intended to mean an emulsion in which the oil is in the discrete phase and the water (aqueous) is the continuous phase.
All ratios, percent, and fractions are on a weight/weight basis and all temperatures are in degrees Celsius unless otherwise expressly stated.
All pressures, unless otherwise expressly stated, are as measured on the APV
homogenizer specified in the Examples section.
Brief Description of Figures Figure 1 depicts the particle size distribution of an emulsion containing 48.9 % by weight of five-fold (5X) orange oil. The curve with squares (^) is of the fresh emulsion with a mean particle size of 0.142 microns. The curve with the smooth line is of a 6-months old emulsion with a mean particle size of 0.151 microns.
Detailed Description of the Invention The present invention pertains to oil-in-water emulsions having a discrete phase volume fraction of 60% to 67% and prepared using at least one low molecular weight surfactant. Such emulsions have excellent emulsion stability, high load, and a small mean particle size of less than 0.2 microns, Further, such emulsions may be produced and used in beverages without a weighting agent.
The at least one low molecular weight (LMW) surfactant is present in an amount of from 2% to 25%, in one embodiment from 8% to 14%, and in yet another embodiment from 12% to 14% (wt/wt) based on the emulsion. In one embodiment, the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate, lecithin, sugar esters, esters of glycerin, and mixtures thereof. In another embodiment, the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate, lecithin, and mixtures thereof, in yet another embodiment is a mixture of quillaja solid extract and polysorbate, and in still another embodiment is a mixture of quillaja and polyoxyethylene (20) sorbitan nmonostearate (Tween 60).
The oil may be any oil used in emulsions, and in one embodiment used in beverage emulsions such as flavor, color, and/or nutrient containing oils, as well as any plant oil, and may be natural or synthetic. In one embodiment, the oil is a fruit oil such as orange oil. In another aspect, the oil contains a nutient such as Vitamin E. In still another embodiment, the oil contains an omega-III fatty acid. The oil is present in a discrete phase volume fraction of from 60 to 67 and in one embodiment is present in in a discrete phase volume fraction of from 62% to 65%. In one embodiment, the volume ratio of LMW surfactant to oil is from 1:2 to 1:5.
The volume fraction of the discrete phase is calculated as set forth in the Examples section.
The emulsion is an oil-in-water emulsion and in one aspect the ratio of the continuous phase to the discrete phase phase is from 40:60 to 33:67 (v/v) and in another embodiment from 38:62 to 35:65 (v/v). The emulsion has a high solids level (discrete phase), and in one embodiment such high solids emulsion may be stored as is and then diluted to the desired solids level with water or other aqueous solvent immediately before or during incorporation into the end use composition, such as a beverage. In the alternative, the high solids emulsion may be diluted prior to storage to enhance the stability.
In one aspect of the invention, the emulsion contains essentially no weighting agents, in one embodiment less than 1% weighting agent, in another embodiment less than 0.5%
weighting agent, in yet another embodiment less than 0.1% weighting agent, and in a further enibodinient 0% weighting agent, all on a weight/weight percentage based on the emulsion.
In still yet another embodiment, the emulsion contains a weighting agent.
The emulsion contains water or an aqueous solution in the continuous phase.
The emulsion may optionally contain additional food grade components. Such food grade componenets include without limitation sugar alcohols or other sugar substitutes, pH agents, salinity agents, colorants and thickeners. In one aspect, the continuous phase contains a preservative and in another the preservative is sodium benzoate.
The emulsions may be prepared using any method of emulsification known in the art.
The emulsions are unique, however, in that the small particle size and excellent stability are achieved by first mixing the ingredients to achieve the desired discrete volume fraction. The mixed ingredients are then homogenized using means known in the art to achieve the desired small mean particle size and/or distribution, Such homogenization is at a pressure of 17 to 65.5 MPa, in one embodiment at a pressure of 31 to 58.6 MPa, and in another embodiment at a pressure of 37.9 to 58.6 MPa, all based on that achieved using the APV
pressure homogenizer detailed in the Examples section. Pressures for other homogenizers may be different, and the skilled practitioner would easily be able to adjust from one homogenizer type to another and determine the equivalent pressure range on each. Further, such small mean particle size and/or distribution may be achieved at such pressures using less than 10 passes, in one embodiment less than 8 passes, and in another embodiment less than 6 passes.
In one embodiment in which polysorbate is used, the polysorbate is melted into a mixture of water and optionally quillaja solid extract, pre-homogenized using high shear, and then homogenized, in one embodiment for 2-6 passes at a pressure of from 17 to 48 MPa.
weighting agent, in yet another embodiment less than 0.1% weighting agent, and in a further enibodinient 0% weighting agent, all on a weight/weight percentage based on the emulsion.
In still yet another embodiment, the emulsion contains a weighting agent.
The emulsion contains water or an aqueous solution in the continuous phase.
The emulsion may optionally contain additional food grade components. Such food grade componenets include without limitation sugar alcohols or other sugar substitutes, pH agents, salinity agents, colorants and thickeners. In one aspect, the continuous phase contains a preservative and in another the preservative is sodium benzoate.
The emulsions may be prepared using any method of emulsification known in the art.
The emulsions are unique, however, in that the small particle size and excellent stability are achieved by first mixing the ingredients to achieve the desired discrete volume fraction. The mixed ingredients are then homogenized using means known in the art to achieve the desired small mean particle size and/or distribution, Such homogenization is at a pressure of 17 to 65.5 MPa, in one embodiment at a pressure of 31 to 58.6 MPa, and in another embodiment at a pressure of 37.9 to 58.6 MPa, all based on that achieved using the APV
pressure homogenizer detailed in the Examples section. Pressures for other homogenizers may be different, and the skilled practitioner would easily be able to adjust from one homogenizer type to another and determine the equivalent pressure range on each. Further, such small mean particle size and/or distribution may be achieved at such pressures using less than 10 passes, in one embodiment less than 8 passes, and in another embodiment less than 6 passes.
In one embodiment in which polysorbate is used, the polysorbate is melted into a mixture of water and optionally quillaja solid extract, pre-homogenized using high shear, and then homogenized, in one embodiment for 2-6 passes at a pressure of from 17 to 48 MPa.
The resultant emulsions have excellent load, in one embodiment at least a 40%
load and in another at least a 50% load, Load is intended to mean the percent ('/w) of the oil on the basis of the emulsifier.
The resultant emulsions have a good emulsion particle size distribution. In one aspect of the invention the mean particle size is between 0. 1 and 0.2 microns, in another embodiment less than 0,2 microns and in yet another embodiment less than 0.15 microns. In another embodiment, at least 90% of the emulsion particles are no greater than 0.2 microns, and in a further embodiment no greater than 0. 15 microns, using the tests set forth in the Examples section. In a still further embodiment, at least 95% of the emulsion particles are no greater than 0.2 microns, and in another embodiment no greater than 0. 15 microns, using the tests set forth in the Examples section.
The resultant beverage emulsions also have excellent stability, such that the the mean particle size remains between 0. 1 and 0.2 microns for at least 3 months, in another embodiment for at least six months and in still another embodiment for at least 12 months at room temperature. Further, in one embodieurt, at least 90% of the emulsion particles remain no greater than 0.2 microns, and in another embodiment no greater than 0. 15 microns for such time, using the tests set forth in the Examples section. In a further embodiment, at least 95% of the emulsion particles remain no greater than 0.2 microns, and in another embodiment no greater than 0.15 microns for such time, using the tests set forth in the Examples section.
The resultant emulsions are useful in a variety of compositions and in one aspect of the invention may be used in any type of beverage. In one embodiment, the emulsions are useful in alcoholic beverages and in yet another embodiment in clear beverages. Clear beverage is intended to mean any beverage with less than 100 Nephelometric Turbidity Units (NTU). The fine particle size and uniform distribution may reduce sediment, creaming, ringing, and/or Ostwald ripening.
Examples The following examples are presented to further illustrate and explain the present invention and should not be taken as limiting in any regard. All ratios, parts and percentages are given by weight and all temperatures in degrees Celsius ( C) unless otherwise noted.
The following materials were used throughout the examples.
Q-NATURALE 200 emulsifier, a liquid quillaja extract which contains about 21%
quillaja solid extract and 14% active saponin, commercially available from National Starch LLC
(Bridgewater, NJ) Tween 60, a polysorbate commercially available from Croda Inc, (Edison, NJ) Orange oil 5X (5 fold) with a density of 0.86 g/ml, commercially available from Givaudan (Cincinati, OH) Pure vegetable oil with a density of 0.93g/ml The following equipment was used through out the examples.
High shear mixer, model I-ISM-I OOLC1, from Ross and Co. (Long Island, NY) Homogenizer, model Gaulin MR 15, from APV (Getzville, NY) Particle size analyzer, Coulter Counter LS320, Beckman Coulter Inc.
(Fullerton, CA) The following procedures were used throughout the examples.
Particle size test Emulsion particle sizes is measured using the LS 13 320, manufactured by Beckman Coulter that incorporates Polarization Intensity Differential Scattering (PIDS) and static light scatting, which covers a particle size range between 0.04 urn to 2000 um.
Using the Beckman Coulter software, version 5.01, the optical parameters for the emulsions as 1.5 for real index of refractions, and 0 for imaginary index of refraction, are entered, Standard procedure is followed in steps as measuring offsets; Alignment;
Background measurement; and sample loading. A diluted sample (diluted to 10% emulsion with water) is then introduced by drops into the sample reservoir while reading in the Measure Loading is observed. When obscuration is in between 40% to 60%, the measurement is started.
When analyzing results, volume fraction is used to generate particle size distribution.
Arithmetic particle size distribution, including for particle size larger than I micron, is obtained by selecting 2, 0.4, 0.7, 1.0 micron in the statistic window.
Determination of volume fraction The volume fraction of the discrete phase is calculated as the sum of the volume fraction of the oil phase plus the volume fraction of the low molecular weight surfactant. The volume fraction of the oil phase is estimated as weight fraction of the oil phase divided by the density of the oil phase. The volume faction of the LMW surfactant and the aqueous phase are estimated as the same as the weight fraction, Example 1 - Preparation of an emulsion of 5- fold Orange Oil with resulting mean particle size of 0.15 microns The volume fraction of the oil and the LMW surfactant, the total discrete phase's volume fraction, and the weight percentage are shown in the table 1. 1.
Table 1.1 Ingredients Weight Percent. Volume fraction.
Orange Oil 5X 48.9% 56.9%
Quillaja solid extract 7.5% 7.5%
Water phase 43.6% 43.6%
Total volume fraction of discrete phase 60%
One kilogram of pre-emulsion was made as follows.
The water phase was prepared by adding Quillaja extract containing 7.5% of Quillaja solid extract to 43.6%. A pre-emulsion was made by slowly adding 48.9% of 5 fold Orange oil to the water phase using an LCI high shear mixer (Model HSM- 100 LCI from Charles Ross & Son Company) at 7500 rpm for 3 minutes.
The above pre-emulsion was homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 44.8 MPa.
The particle size of the emulsion was then checked. The emulsion's mean particle size was 0.142 microns.
After 6 months storage, the room temperature emulsion of the present invention was stable and had a mean particle size of 0.151 microns.
Example 2 - Preparation of emulsions of Vegetable Oil with resulting mean particle size of less than 0.2 microns The volume fraction of each ingredient and the total volume fraction of the discrete phase of all three samples are shown in the table 2.1 and the weight percentages of all three samples are shown in table 2.2.
load and in another at least a 50% load, Load is intended to mean the percent ('/w) of the oil on the basis of the emulsifier.
The resultant emulsions have a good emulsion particle size distribution. In one aspect of the invention the mean particle size is between 0. 1 and 0.2 microns, in another embodiment less than 0,2 microns and in yet another embodiment less than 0.15 microns. In another embodiment, at least 90% of the emulsion particles are no greater than 0.2 microns, and in a further embodiment no greater than 0. 15 microns, using the tests set forth in the Examples section. In a still further embodiment, at least 95% of the emulsion particles are no greater than 0.2 microns, and in another embodiment no greater than 0. 15 microns, using the tests set forth in the Examples section.
The resultant beverage emulsions also have excellent stability, such that the the mean particle size remains between 0. 1 and 0.2 microns for at least 3 months, in another embodiment for at least six months and in still another embodiment for at least 12 months at room temperature. Further, in one embodieurt, at least 90% of the emulsion particles remain no greater than 0.2 microns, and in another embodiment no greater than 0. 15 microns for such time, using the tests set forth in the Examples section. In a further embodiment, at least 95% of the emulsion particles remain no greater than 0.2 microns, and in another embodiment no greater than 0.15 microns for such time, using the tests set forth in the Examples section.
The resultant emulsions are useful in a variety of compositions and in one aspect of the invention may be used in any type of beverage. In one embodiment, the emulsions are useful in alcoholic beverages and in yet another embodiment in clear beverages. Clear beverage is intended to mean any beverage with less than 100 Nephelometric Turbidity Units (NTU). The fine particle size and uniform distribution may reduce sediment, creaming, ringing, and/or Ostwald ripening.
Examples The following examples are presented to further illustrate and explain the present invention and should not be taken as limiting in any regard. All ratios, parts and percentages are given by weight and all temperatures in degrees Celsius ( C) unless otherwise noted.
The following materials were used throughout the examples.
Q-NATURALE 200 emulsifier, a liquid quillaja extract which contains about 21%
quillaja solid extract and 14% active saponin, commercially available from National Starch LLC
(Bridgewater, NJ) Tween 60, a polysorbate commercially available from Croda Inc, (Edison, NJ) Orange oil 5X (5 fold) with a density of 0.86 g/ml, commercially available from Givaudan (Cincinati, OH) Pure vegetable oil with a density of 0.93g/ml The following equipment was used through out the examples.
High shear mixer, model I-ISM-I OOLC1, from Ross and Co. (Long Island, NY) Homogenizer, model Gaulin MR 15, from APV (Getzville, NY) Particle size analyzer, Coulter Counter LS320, Beckman Coulter Inc.
(Fullerton, CA) The following procedures were used throughout the examples.
Particle size test Emulsion particle sizes is measured using the LS 13 320, manufactured by Beckman Coulter that incorporates Polarization Intensity Differential Scattering (PIDS) and static light scatting, which covers a particle size range between 0.04 urn to 2000 um.
Using the Beckman Coulter software, version 5.01, the optical parameters for the emulsions as 1.5 for real index of refractions, and 0 for imaginary index of refraction, are entered, Standard procedure is followed in steps as measuring offsets; Alignment;
Background measurement; and sample loading. A diluted sample (diluted to 10% emulsion with water) is then introduced by drops into the sample reservoir while reading in the Measure Loading is observed. When obscuration is in between 40% to 60%, the measurement is started.
When analyzing results, volume fraction is used to generate particle size distribution.
Arithmetic particle size distribution, including for particle size larger than I micron, is obtained by selecting 2, 0.4, 0.7, 1.0 micron in the statistic window.
Determination of volume fraction The volume fraction of the discrete phase is calculated as the sum of the volume fraction of the oil phase plus the volume fraction of the low molecular weight surfactant. The volume fraction of the oil phase is estimated as weight fraction of the oil phase divided by the density of the oil phase. The volume faction of the LMW surfactant and the aqueous phase are estimated as the same as the weight fraction, Example 1 - Preparation of an emulsion of 5- fold Orange Oil with resulting mean particle size of 0.15 microns The volume fraction of the oil and the LMW surfactant, the total discrete phase's volume fraction, and the weight percentage are shown in the table 1. 1.
Table 1.1 Ingredients Weight Percent. Volume fraction.
Orange Oil 5X 48.9% 56.9%
Quillaja solid extract 7.5% 7.5%
Water phase 43.6% 43.6%
Total volume fraction of discrete phase 60%
One kilogram of pre-emulsion was made as follows.
The water phase was prepared by adding Quillaja extract containing 7.5% of Quillaja solid extract to 43.6%. A pre-emulsion was made by slowly adding 48.9% of 5 fold Orange oil to the water phase using an LCI high shear mixer (Model HSM- 100 LCI from Charles Ross & Son Company) at 7500 rpm for 3 minutes.
The above pre-emulsion was homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 44.8 MPa.
The particle size of the emulsion was then checked. The emulsion's mean particle size was 0.142 microns.
After 6 months storage, the room temperature emulsion of the present invention was stable and had a mean particle size of 0.151 microns.
Example 2 - Preparation of emulsions of Vegetable Oil with resulting mean particle size of less than 0.2 microns The volume fraction of each ingredient and the total volume fraction of the discrete phase of all three samples are shown in the table 2.1 and the weight percentages of all three samples are shown in table 2.2.
Table 2.1 Volume fraction Ingredients Sample 1 Sample 2 Sample 3 Vegetable oil 53% 52% 53%
Tween 60 12% 10% 11%
Total discrete phase 65 % 62% 64%
volume fraction Table 2.2 Weight percentage Ingredients Sample 1 Sample 2 Sample 3 Vegetable oil 49% 48% 49%
Tween 60 12% 10% 11%
Water 39% 42% 40%
One kilogram of pre-emulsion was made as follows.
Tween 60 was heated to 65 C to be fully liquefied. The water phase was prepared by adding 12%, 10%, or I I% of liquefied Tween 60 to 60 C water at the amount of 39%, 42%, and 40% for sample 1, 2, and 3 respectively. The pre-emulsion were made by slowly adding the vegetable oil to the water phase using an LCI high shear mixer (Model HSM-from Charles Ross & Son Company) at 10000 rpin for 3 minutes. The above pre-emulsion was homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 58.6 MPa. The particle size of the emulsion was then checked at day 0 and every month after for 12 months. After 12 months storage, the room temperature emulsions of the present invention were stable. The mean particle size results are shown in table 2.3.
Table 2.3 Mean Particle Size micron) Da 0 1 year Sample 1 0.158 0.163 Sample 2 0.154 0.171 Sample 3 0.139 0.142 Example 3 - Comparison of emulsions of 5 fold Oil with discrete phase volume fraction outside the claimed range Both volume fraction of the ingredients and total volume fraction of discrete phase of all 4 samples are shown in table 3.1. The weight percentages of all of the ingredients are shown in table 3,2 Table 3.1 Volume fraction Ingredients Sample I Sample 2 Sample 3 Sample 4 5 fold Orange oil 33% 38% 43% 51%
Tween 60 4% 12% 15% 17%
Quillaja Solid extract 0.84% 1.73% 0.84% 2%
Total discrete phase 37.84% 51.73% 58.84% 70%
volume fraction Table 3.2 Weight percentage Ingredients Sample 1 Sample 2 Sample 3 Sample 4 5 fold Orange oil 28.38% 32.98% 36,98% 43.86%
Tween 60 4% 12% 15% 17%
Quillaja Solid extract 0.84% 1.73% 0.84% 2%
Water 66.78% 53.59% 47.18% 36.14%
One kilogram of pre-emulsion was made as follows.
Tween 60 was heated to 65 C to be fully liquefied. The water phase was prepared by adding the liquefied Tween 60 (4%, 12%, 15%, or 17%) and Quillaja solid extract (0.84%, 1.73%, 0.84%, or 2%) to 60 C water (66.78%, 53.59%, 47.18% or 37.14%) for samples 1, 2, 3 and 4 respectively. The pre-emulsions were made by slowly adding the needed 5 fold Orange oil (28.38%, 32.68%, 36.98% or 43.86%) to the water phase using an LCI
high shear mixer (Model HSM- 100 LCI from Charles Ross & Son Company) at 7500 rpm for 3 minutes.
Sample 4's pre-emulsion was extremely viscous with a pudding-like thickness:
it was not able to be run successfully through the homogenizer. The other pre-emulsions were homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 44,8 MPa. The particle size of the emulsions was then checked. The mean particle size results are shown in table 3.3.
Table 3.3 Mean particle size (micron) - day 0 Sample 1 0. 822 Sample 2 0..656 Sample 3 0.393
Tween 60 12% 10% 11%
Total discrete phase 65 % 62% 64%
volume fraction Table 2.2 Weight percentage Ingredients Sample 1 Sample 2 Sample 3 Vegetable oil 49% 48% 49%
Tween 60 12% 10% 11%
Water 39% 42% 40%
One kilogram of pre-emulsion was made as follows.
Tween 60 was heated to 65 C to be fully liquefied. The water phase was prepared by adding 12%, 10%, or I I% of liquefied Tween 60 to 60 C water at the amount of 39%, 42%, and 40% for sample 1, 2, and 3 respectively. The pre-emulsion were made by slowly adding the vegetable oil to the water phase using an LCI high shear mixer (Model HSM-from Charles Ross & Son Company) at 10000 rpin for 3 minutes. The above pre-emulsion was homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 58.6 MPa. The particle size of the emulsion was then checked at day 0 and every month after for 12 months. After 12 months storage, the room temperature emulsions of the present invention were stable. The mean particle size results are shown in table 2.3.
Table 2.3 Mean Particle Size micron) Da 0 1 year Sample 1 0.158 0.163 Sample 2 0.154 0.171 Sample 3 0.139 0.142 Example 3 - Comparison of emulsions of 5 fold Oil with discrete phase volume fraction outside the claimed range Both volume fraction of the ingredients and total volume fraction of discrete phase of all 4 samples are shown in table 3.1. The weight percentages of all of the ingredients are shown in table 3,2 Table 3.1 Volume fraction Ingredients Sample I Sample 2 Sample 3 Sample 4 5 fold Orange oil 33% 38% 43% 51%
Tween 60 4% 12% 15% 17%
Quillaja Solid extract 0.84% 1.73% 0.84% 2%
Total discrete phase 37.84% 51.73% 58.84% 70%
volume fraction Table 3.2 Weight percentage Ingredients Sample 1 Sample 2 Sample 3 Sample 4 5 fold Orange oil 28.38% 32.98% 36,98% 43.86%
Tween 60 4% 12% 15% 17%
Quillaja Solid extract 0.84% 1.73% 0.84% 2%
Water 66.78% 53.59% 47.18% 36.14%
One kilogram of pre-emulsion was made as follows.
Tween 60 was heated to 65 C to be fully liquefied. The water phase was prepared by adding the liquefied Tween 60 (4%, 12%, 15%, or 17%) and Quillaja solid extract (0.84%, 1.73%, 0.84%, or 2%) to 60 C water (66.78%, 53.59%, 47.18% or 37.14%) for samples 1, 2, 3 and 4 respectively. The pre-emulsions were made by slowly adding the needed 5 fold Orange oil (28.38%, 32.68%, 36.98% or 43.86%) to the water phase using an LCI
high shear mixer (Model HSM- 100 LCI from Charles Ross & Son Company) at 7500 rpm for 3 minutes.
Sample 4's pre-emulsion was extremely viscous with a pudding-like thickness:
it was not able to be run successfully through the homogenizer. The other pre-emulsions were homogenized using an APV pressure homogenizer (Model 15 MR Laboratory Homogenizer from APV Gaulin) for 3 passes at 44,8 MPa. The particle size of the emulsions was then checked. The mean particle size results are shown in table 3.3.
Table 3.3 Mean particle size (micron) - day 0 Sample 1 0. 822 Sample 2 0..656 Sample 3 0.393
Claims (20)
1. An oil-in-water emulsion comprising;
a. a water-containing continuous phase;
b. an oil-containing discrete phase; and c. at least one low molecular weight surfactant;
wherein the volume fraction of the discrete phase is from 60% to 67% and the emulsion has a mean particle size of less than 0.2 microns.
a. a water-containing continuous phase;
b. an oil-containing discrete phase; and c. at least one low molecular weight surfactant;
wherein the volume fraction of the discrete phase is from 60% to 67% and the emulsion has a mean particle size of less than 0.2 microns.
2. The emulsion of claim 1, wherein the volume fraction of the discrete phase is from 62% to 65%.
3. The emulsion of claim 1 or 2, wherein the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate and lecithin.
4. The emulsion of claim 3, wherein the low molecular weight surfactant is quillaja solid extract and polysorbate.
5. The emulsion of claim 4, wherein the polysorbate is polyoxyethylene (20) sorbitan monostearate (Tween 60).
6. The emulsion of any one of claims 1-5, wherein the mean particle size of the emulsion is less than 0.15 microns.
7. The emulsion of any one of claims 1-6, wherein at least 90% of the emulsion particles are no greater than 0.2 microns.
8. The emulsion of claim 7, wherein at least 90% of the emulsion particles are no greater than 0.15 microns.
9. The emulsion of any one of claims 1-8, wherein the emulsion is stable such that the the mean particle size remains less than 0.2 microns for at least 3 months.
10. The emulsion of claim 9, wherein the emulsion is stable such that the the mean particle size remains less than 0.2 microns for at least 6 months.
11. The emulsion of claim 9, wherein the emulsion is stable such that the the mean particle size remains less than 0.2 microns for at least 12 months.
12. The emulsion of any one of claims 1-11, in which the emulsion is a non-weighted emulsion.
13. A method of making an oil-in-water emulsion comprising:
a. mixing water, oil and at least one LMW surfactant to obtain a volume fraction of the discrete phase from 60-67; and b. homogenizing with less than 10 passes at a pressure of 17 to 65.5 MPascals;
to result in an oil-in-water emulsion with a mean particle size of less than 0.2 microns.
a. mixing water, oil and at least one LMW surfactant to obtain a volume fraction of the discrete phase from 60-67; and b. homogenizing with less than 10 passes at a pressure of 17 to 65.5 MPascals;
to result in an oil-in-water emulsion with a mean particle size of less than 0.2 microns.
14. The method of claim 13, wherein the volume fraction of the discrete phase is from 62 to 65.
15. The method of 13 or 14, wherein the low molecular weight surfactant is selected from the group consisting of quillaja solid extract, polysorbate and lecithin.
16. The method of claim 15, wherein the low molecular weight surfactant is quillaja solid extract and polysorbate.
17. The method of claim 16, wherein the polysorbate is polyoxyethylene (20) sorbitan monostearate (Tween 60).
18. The method of any one of claims 13-17, wherein the mean particle size of the emulsion is between 0.1 and 0.2 microns.
19. The method of any one of claims 13-18, wherein at least 90% of the emulsion particles are no greater than 0.2 microns.
20. The method of claim 19, wherein at least 90% of the emulsion particles are no greater than 0.15 microns.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12/748,013 | 2010-03-26 | ||
| US12/748,013 US8318233B2 (en) | 2010-03-26 | 2010-03-26 | Emulsions useful in beverages |
| PCT/US2011/026265 WO2011119290A1 (en) | 2010-03-26 | 2011-02-25 | Emulsions useful in beverages |
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| CA2794251A1 true CA2794251A1 (en) | 2011-09-29 |
| CA2794251C CA2794251C (en) | 2016-08-16 |
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| US (1) | US8318233B2 (en) |
| EP (1) | EP2552236B1 (en) |
| JP (1) | JP5775145B2 (en) |
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Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2359698B1 (en) * | 2010-01-22 | 2013-12-04 | Symrise AG | Compositions with a surfactant system comprising saponins, and lecithin |
| GB201204377D0 (en) * | 2012-03-13 | 2012-04-25 | Givaudan Sa | Composition |
| EP2846647A1 (en) | 2012-05-11 | 2015-03-18 | Chr. Hansen A/S | A composition comprising chlorophyllin as a green pigment |
| WO2013171108A1 (en) | 2012-05-16 | 2013-11-21 | Chr. Hansen A/S | A composition comprising norbixin as an orange/red pigment |
| US20130323379A1 (en) * | 2012-05-31 | 2013-12-05 | Pepsico, Inc. | Natural clouding system for beverage applications |
| AU2013206558A1 (en) * | 2012-06-22 | 2014-01-16 | Atlas Pearls And Perfumes Ltd | Pearl Treatment Composition and Method |
| WO2014140268A1 (en) * | 2013-03-15 | 2014-09-18 | Dsm Ip Assets B. V. | Solid lipid nanoparticles (ii) |
| EP2777402A1 (en) * | 2013-03-15 | 2014-09-17 | DSM IP Assets B.V. | Solid lipid nanoparticles (I) |
| RU2665931C2 (en) * | 2013-06-21 | 2018-09-05 | Фирмениш Са | Preparation of dried particles containing menthol |
| US8828457B1 (en) | 2013-06-28 | 2014-09-09 | Dr Pepper/Seven Up, Inc. | Emulsions providing stable vitamin compositions and methods of forming compositions thereof |
| US9907325B2 (en) * | 2015-03-06 | 2018-03-06 | Kraft Foods Group Brands Llc | Encapsulated weighting agents for beverage emulsions |
| EP3097790B1 (en) * | 2015-05-26 | 2018-05-16 | Symrise AG | Turbid beverages with improved storage stabiliy |
| US20170143011A1 (en) * | 2015-11-25 | 2017-05-25 | Pepsico, Inc. | Beverage nanoemulstions produced by high shear processing |
| WO2017140376A1 (en) | 2016-02-19 | 2017-08-24 | Symrise Ag | Consumable emulsion |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4284655A (en) * | 1980-04-22 | 1981-08-18 | Scm Corporation | Low-fat comestible spread substitutes |
| USRE31754E (en) * | 1980-04-22 | 1984-12-04 | Scm Corporation | Low-fat comestible spread substitutes |
| JPS60190224A (en) | 1984-03-13 | 1985-09-27 | Maruzen Kasei Kk | Surfactant |
| JPS6211541A (en) | 1985-07-08 | 1987-01-20 | Maruzen Kasei Kk | Oil-in-water type emulsion |
| US4705691A (en) * | 1985-11-18 | 1987-11-10 | The Procter & Gamble Co. | Beverage opacifier |
| JPS6398369A (en) | 1986-10-14 | 1988-04-28 | Maruzen Kasei Kk | Cloud for drink |
| JPS63157934A (en) | 1986-12-20 | 1988-06-30 | Nippon Oil & Fats Co Ltd | O/w-type emulsion composition |
| JPH02238869A (en) | 1989-03-10 | 1990-09-21 | Eiichi Tashiro | Saponaceous beverage |
| JP2895088B2 (en) | 1989-03-31 | 1999-05-24 | 明治乳業株式会社 | Surfactants and their use |
| JP2741093B2 (en) * | 1990-06-14 | 1998-04-15 | 長谷川香料株式会社 | Production method of emulsion composition for food and drink |
| JP2950348B2 (en) * | 1991-04-27 | 1999-09-20 | 吉富製薬株式会社 | Fat emulsion and method for producing the same |
| JPH0538275A (en) | 1991-05-31 | 1993-02-19 | Godo Shiyusei Kk | Production of fomable fancy drink |
| JPH0622697A (en) | 1991-10-17 | 1994-02-01 | T Hasegawa Co Ltd | Method for increasing flavor and taste of candies |
| JPH0851928A (en) | 1994-08-12 | 1996-02-27 | Nippon Suisan Kaisha Ltd | Emulsified oil and fat excellent in stability against oxidation and having transparency and food added with thereof |
| US5616358A (en) | 1995-07-19 | 1997-04-01 | The Procter & Gamble Company | Stable beverages containing emulsion with unweighted oil and process of making |
| JP3528382B2 (en) * | 1995-12-20 | 2004-05-17 | 日本油脂株式会社 | Fat and oil solubilizing composition, method for producing the same, and food and drink containing the same |
| US6214349B1 (en) | 1996-03-12 | 2001-04-10 | Nature's Sunshine Products, Inc. | Composition for limiting the assimilation of dietary fat and methods of making and using same |
| CZ295169B6 (en) * | 2000-10-27 | 2005-06-15 | Unilever N. V. | Food composition in the form of emulsion |
| US6902756B2 (en) * | 2001-04-02 | 2005-06-07 | Firmenich Sa | Transparent high oil loaded microemulsions |
| JP2002320447A (en) * | 2001-04-26 | 2002-11-05 | Sanei Gen Ffi Inc | Glycolipid-containing emulsified composition |
| EP1549159B1 (en) * | 2002-06-12 | 2008-11-12 | The Coca-Cola Company | Beverages containing plant sterols |
| AU2003238264B2 (en) * | 2002-06-18 | 2009-05-21 | Dsm Ip Assets B.V. | Stable emulsions of oils in aqueous solutions and methods for producing same |
| JP4304940B2 (en) | 2002-08-30 | 2009-07-29 | 有限会社ビオメディクス | Propolis extract-containing composition for water dispersion and beverage |
| NO317310B1 (en) * | 2003-02-28 | 2004-10-04 | Bioli Innovation As | Oil-in-water emulsion concentrate for nutritional formula and its use. |
| FR2857012B1 (en) * | 2003-07-02 | 2006-02-03 | Univ Toulouse | NOVEL AROMATIC INHIBITOR COMPOUNDS OF ALDOLASES, PROCESS FOR SYNTHESIS AND APPLICATIONS |
| ES2300838T3 (en) * | 2003-10-30 | 2008-06-16 | Lipid Nutrition B.V. | FOOD PRODUCT CONTAINING EXTRACT OF PINE NEEDLES. |
| JP4420658B2 (en) | 2003-12-04 | 2010-02-24 | 小川香料株式会社 | Sugar coating method and emulsified fragrance and syrup used therefor |
| CA2587484A1 (en) * | 2004-11-16 | 2006-05-26 | Unilever Plc | Satiety emulsions and food compositions |
| JP2006271279A (en) * | 2005-03-29 | 2006-10-12 | Kaneka Corp | Oil-in-water emulsified oil and fat composition |
| AU2006243463A1 (en) * | 2005-05-04 | 2006-11-09 | Unilever Plc | Satiety emulsions and food compositions |
| US20070014819A1 (en) * | 2005-07-13 | 2007-01-18 | Weckteck Biotechnology Company Limited | Method of emulsifying phytosterol by natural saponin,emulsion prepared thereby and water dispersible phytosterol powder product |
| EP1924158B1 (en) * | 2005-09-02 | 2010-06-02 | Firmenich S.A. | Clear flavor microemulsions comprising sugar esters of fatty acids |
| US8153180B2 (en) * | 2005-09-06 | 2012-04-10 | Pepsico, Inc. | Method and apparatus for making beverages |
| BRPI0617002A2 (en) * | 2005-09-09 | 2011-07-05 | Loc Aid Technologies Inc | location-based application development system, portal to enable third-party location-based applications and method for developing a location-based application for use by a mobile device |
| ZA200803996B (en) * | 2005-11-14 | 2009-10-28 | Unilever Plc | A mayonnaise product and a process for preparing it |
| BRPI0618834A2 (en) * | 2005-11-22 | 2011-09-13 | Nestec Sa | easily dispersible lipid phase |
| US20080058418A1 (en) | 2006-09-06 | 2008-03-06 | The Coca-Cola Company | Stable polyunsaturated fatty acid emulsions and methods for inhibiting, suppressing, or reducing degradation of polyunsaturated fatty acids in an emulsion |
| JP4302159B2 (en) * | 2006-12-01 | 2009-07-22 | 富士フイルム株式会社 | Emulsion composition, food and cosmetic containing the emulsion composition |
| US20080148626A1 (en) | 2006-12-20 | 2008-06-26 | Diamond Qc Technologies Inc. | Multiple polydispersed fuel emulsion |
| DE202007003800U1 (en) * | 2007-03-14 | 2008-07-17 | Sensient Food Colors Germany Gmbh & Co. Kg | Dye emulsion |
| JP2008280257A (en) * | 2007-05-08 | 2008-11-20 | Fujifilm Corp | Emulsion composition and method for preventing agglomeration of polyphenol compound |
| WO2008140065A2 (en) | 2007-05-08 | 2008-11-20 | Fujifilm Corporation | Emulsion-containing composition, food and topical product, and method of preventing coagulation of polyphenol compound |
| JP2008280256A (en) * | 2007-05-08 | 2008-11-20 | Fujifilm Corp | Emulsion-containing composition, foodstuff and preparation for external use |
| KR100991675B1 (en) | 2007-08-06 | 2010-11-04 | 한국식품연구원 | Nanoemulsion and nanoparticle containing plant essential oil and method of production thereof |
| WO2009067734A1 (en) * | 2007-11-28 | 2009-06-04 | Commonwealth Scientific And Industrial Research Organisation | Nanoemulsions |
| WO2009090249A1 (en) * | 2008-01-18 | 2009-07-23 | Dsm Ip Assets B.V. | Spray-dried emulsion |
| US8337931B2 (en) | 2008-06-23 | 2012-12-25 | Virun, Inc. | Compositions containing non-polar compounds |
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| RU2528705C2 (en) | 2014-09-20 |
| JP2013526847A (en) | 2013-06-27 |
| US8318233B2 (en) | 2012-11-27 |
| MX2012010974A (en) | 2013-04-03 |
| BR112012024131B1 (en) | 2018-08-14 |
| CN102834023B (en) | 2015-03-25 |
| CN102834023A (en) | 2012-12-19 |
| JP5775145B2 (en) | 2015-09-09 |
| EP2552236B1 (en) | 2017-05-10 |
| EP2552236A1 (en) | 2013-02-06 |
| WO2011119290A1 (en) | 2011-09-29 |
| US20110236558A1 (en) | 2011-09-29 |
| BR112012024131A2 (en) | 2015-09-01 |
| CA2794251C (en) | 2016-08-16 |
| DK2552236T3 (en) | 2017-08-28 |
| AU2011229890A1 (en) | 2012-10-18 |
| AU2011229890B2 (en) | 2013-09-19 |
| PL2552236T3 (en) | 2017-10-31 |
| ES2636666T3 (en) | 2017-10-06 |
| RU2012145455A (en) | 2014-05-10 |
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